Organic electronic element comprising compound for organic electronic element and an electronic device thereof

ABSTRACT

Provided are an organic electronic element including an anode, a cathode, and an organic material layer between the anode and the cathode, and an electronic device including the organic electronic element, wherein the organic material layer includes each of the compounds represented by Formulas 1 and 2 and the driving voltage of the organic electronic element is lowered, and the luminous efficiency and lifetime of the element are improved.

TECHNICAL FIELD

The present invention relates to compound for organic electronicelement, organic electronic element using the same, and an electronicdevice thereof.

BACKGROUND ART

In general, organic light emitting phenomenon refers to a phenomenonthat converts electric energy into light energy by using an organicmaterial. An organic electronic element using an organic light emittingphenomenon usually has a structure including an anode, a cathode, and anorganic material layer interposed therebetween. Here, in order toincrease the efficiency and stability of the organic electronic element,the organic material layer is often composed of a multi-layeredstructure composed of different materials, and for example, may includea hole injection layer, a hole transport layer, an emitting layer, anelectron transport layer, an electron injection layer and the like.

A material used as an organic material layer in an organic electronicelement may be classified into a light emitting material and a chargetransport material, such as a hole injection material, a hole transportmaterial, an electron transport material, an electron injection materialand the like depending on its function.

In the organic light emitting diode, the most problematic is thelifetime and the efficiency. As the display becomes large, theefficiency and the lifetime problem must be solved. Efficiency, lifespan, driving voltage and the like are related to each other. As theefficiency is increased, the driving voltage is relatively decreased,and as the driving voltage drops, the crystallization of the organicmaterial due to joule heating generated during driving is reduced, andas a result, the life span tends to increase.

However, simply improving the organic material layer cannot maximize theefficiency. This is because, when the optimal combination of the energylevel and T1 value between each organic material layer and the intrinsicproperties (mobility, interface characteristics, etc.) of the materialare achieved, long life and high efficiency can be achieved at the sametime.

Further, recently, in organic electroluminescent devices, in order tosolve the emission problem in a hole transport layer, anemitting-auxiliary layer must be present between the hole transportlayer and an emitting layer, and it is necessary to develop differentemitting-auxiliary layers according to the respective emitting layers(R, G, B).

In general, electrons are transferred from the electron transport layerto the emitting layer, and holes are transferred from the hole transportlayer to the emitting layer to generate excitons by recombination.

However, the material used for the hole transport layer has a low HOMOvalue and therefore has mostly low T1 value. As a result, the excitongenerated in the emitting layer is transferred to the hole transportlayer, resulting in charge unbalance in the emitting layer, and light isemitted at the interface of the hole transport layer.

When light is emitted at the interface of the hole transport layer, thecolor purity and efficiency of the organic electronic device are loweredand the life span is shortened. Therefore, it is urgently required todevelop an emitting-auxiliary layer having a high T1 value and a HOMOlevel between the HOMO energy level of the hole transport layer and theHOMO energy level of the emitting layer.

Meanwhile, it is necessary to develop a hole injection layer materialhaving stable characteristics, that is, a high glass transitiontemperature, against joule heating generated when the device is driven,while delaying penetration of the metal oxide from the anode electrode(ITO), which is one of the causes of shortening the lifetime of theorganic electronic device, into the organic layer. The low glasstransition temperature of the hole transport layer material has acharacteristic that when the device is driven, the uniformity of thesurface of the thin film is lowered, which has been reported to have agreat influence on the lifetime of the device. In addition, OLED devicesare mainly formed by a deposition method, and it is necessary to developa material that can withstand long time in deposition, that is, amaterial having high heat resistance characteristics.

That is, in order to sufficiently exhibit the excellent characteristicsof the organic electronic element, a material for forming an organicmaterial layer in an element such as a hole injection material, a holetransport material, a light emitting material, an electron transportmaterial, an electron injection material, an emitting-auxiliary layermaterial should be supported by stable and efficient materials. However,such a stable and efficient organic material layer material for anorganic electronic element has not been sufficiently developed yet.Therefore, development of new materials is continuously required, anddevelopment of materials for the hole transport layer or theemitting-auxiliary layer is urgently required.

SUMMARY OF INVENTION Problems to be Solved by the Invention

An object of the present invention is to provide an organic electronicelement including a compound capable of lowering a driving voltage of anelement and improving luminous efficiency, color purity, stability, andlifetime of the element, and an electronic element thereof.

The present invention provides an organic electronic element comprisinga first electrode, a second electrode, and an organic material layerformed between the first electrode and the second electrode, wherein theorganic material layer comprises an emitting layer, wherein the emittinglayer is a phosphorescent emitting layer and comprises a first hostcompound represented by Formula 1 and a second host compound representedby Formula 2.

In another aspect, the present invention provides an electronic deviceincluding the organic electronic element.

Effects of the Invention

By using the compound according to the present invention, it is possibleto achieve a high luminous efficiency, a low driving voltage, and a highheat resistance of the element, and can greatly improve the color purityand lifetime of the element.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 to FIG. 3 are each an exemplary view of an organic electronicelement according to one aspect of the present invention.

DETAILED DESCRIPTION OF THE INVENTION

Hereinafter, some embodiments of the present invention will be describedin detail. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif a component is described as being “connected”, “coupled”, or“connected” to another component, the component may be directlyconnected or connected to the other component, but another component maybe “connected,” coupled” or “connected” between each component.

As used in the specification and the accompanying claims, unlessotherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen”, as used herein,includes fluorine, bromine, chlorine, or iodine.

Unless otherwise stated, the term “alkyl” or “alkyl group”, as usedherein, has a single bond of 1 to 60 carbon atoms, and means saturatedaliphatic functional radicals including a linear alkyl group, a branchedchain alkyl group, a cycloalkyl group (alicyclic), an cycloalkyl groupsubstituted with a alkyl or an alkyl group substituted with acycloalkyl.

Unless otherwise stated, the term “alkenyl” or “alkynyl”, as usedherein, has double or triple bonds of 2 to 60 carbon atoms, but is notlimited thereto, and includes a linear or a branched chain group.

Unless otherwise stated, the term “cycloalkyl”, as used herein, meansalkyl forming a ring having 3 to 60 carbon atoms, but is not limitedthereto.

Unless otherwise stated, the term “alkoxyl group”, “alkoxy group” or“alkyloxy group”, as used herein, means an oxygen radical attached to analkyl group, but is not limited thereto, and has 1 to 60 carbon atoms.

Unless otherwise stated, the term “aryloxyl group” or “aryloxy group”,as used herein, means an oxygen radical attached to an aryl group, butis not limited thereto, and has 6 to 60 carbon atoms.

Unless otherwise stated, the term “aryl group” or “arylene group”, asused herein, has 6 to 60 carbon atoms, but is not limited thereto.Herein, the aryl group or arylene group means a monocyclic andpolycyclic aromatic group, and may also be formed in conjunction with anadjacent group. Examples of “aryl group” may include a phenyl group, abiphenyl group, a fluorene group, or a spirofluorene group.

The prefix “aryl” or “ar” means a radical substituted with an arylgroup. For example, an arylalkyl may be an alkyl substituted with anaryl, and an arylalenyl may be an alkenyl substituted with aryl, and aradical substituted with an aryl has a number of carbon atoms as definedherein.

Also, when prefixes are named subsequently, it means that substituentsare listed in the order described first. For example, an arylalkoxymeans an alkoxy substituted with an aryl, an alkoxylcarbonyl means acarbonyl substituted with an alkoxyl, and an arylcarbonylalkenyl alsomeans an alkenyl substituted with an arylcarbonyl, wherein thearylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the term “heterocyclic group”, as used herein,contains one or more heteroatoms, but is not limited thereto, has 2 to60 carbon atoms, includes any one of monocyclic and polycyclic rings,and may include heteroaliphadic ring and/or heteroaromatic ring. Also,the heterocyclic group may also be formed in conjunction with anadjacent group.

Unless otherwise stated, the term “heteroatom”, as used herein,represents at least one of N, O, S, P, or Si.

Also, the term “heterocyclic group” may include a ring including SO₂instead of carbon consisting of cycle. For example, “heterocyclic group”includes the following compound.

Unless otherwise stated, the term “fluorenyl group” or “fluorenylenegroup”, as used herein, means a monovalent or divalent functional group,in which R, R′ and R″ are all hydrogen in the following structures, andthe term “substituted fluorenyl group” or “substituted fluorenylenegroup” means that at least one of the substituents R, R′, R″ is asubstituent other than hydrogen, and include those in which R and R′ arebonded to each other to form a Spiro compound together with the carbonto which they are bonded.

The term “spiro compound”, as used herein, has a ‘Spiro union’, and aSpiro union means a connection in which two rings share only one atom.At this time, atoms shared in the two rings are called ‘spiro atoms’,and these compounds are called ‘monospiro-’, ‘di-spiro-’ and‘tri-spiro-’, respectively, depending on the number of atoms in acompound.

Unless otherwise stated, the term “aliphatic”, as used herein, means analiphatic hydrocarbon having 1 to 60 carbon atoms, and the term“aliphatic ring”, as used herein, means an aliphatic hydrocarbon ringhaving 3 to 60 carbon atoms.

Unless otherwise stated, the term “ring”, as used herein, means analiphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6to 60 carbon atoms, or a hetero ring having 2 to 60 carbon atoms, or afused ring formed by the combination of them, and includes a saturatedor unsaturated ring.

Other hetero compounds or hetero radicals other than the above-mentionedhetero compounds include, but are not limited thereto, one or moreheteroatoms.

Unless otherwise stated, the term “substituted or unsubstituted”, asused herein, means that substitution is substituted by at least onesubstituent selected from the group consisting of, but is not limitedthereto, deuterium, halogen, an amino group, a nitrile group, a nitrogroup, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkylaminegroup, a C₁-C₂₀ alkylthiopen group, a C₆-C₂₀ arylthiopen group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, a C₃-C₂₀ cycloalkyl group, aC₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted by deuterium, aC₈-C₂₀ arylalkenyl group, a silane group, a boron group, a germaniumgroup, and a C₂-C₂₀ heterocyclic group.

Unless otherwise expressly stated, the Formula used in the presentinvention, as used herein, is applied in the same manner as thesubstituent definition according to the definition of the exponent ofthe following Formula.

here, when a is an integer of zero, the substituent R¹ is absent, when ais an integer of 1, the sole substituent R¹ is linked to any one of thecarbon constituting the benzene ring, when a is an integer of 2 or 3,each substituent R¹s may be the same and different, when a is an integerof 4 to 6, and is linked to the benzene ring in a similar manner,whereas the indication of hydrogen bound to the carbon forming thebenzene ring is omitted.

Hereinafter, a laminated structure of an organic electronic deviceincluding the compound of the present invention will be described withreference to FIGS. 1 to 3.

In adding reference numerals to elements of each figure, it should benoted that the same elements have the same numerals as possible even ifthey are indicated on different figures.

In addition, in describing the present invention, when it is determinedthat a detailed description of a related known configuration or functionmay obscure the subject matter of the present invention, a detaileddescription thereof will be omitted.

FIG. 1 to FIG. 3 illustrate an example of an organic electronic elementaccording to an embodiment of the present invention.

Referring to FIG. 1, an organic electronic element (100) according to anembodiment of the present invention includes a first electrode (110), asecond electrode (170) formed on a substrate (not shown) and an organicmaterial layer formed between the first electrode (110) and the secondelectrode (170).

The first electrode (110) may be an anode, the second electrode (170)may be a cathode, and in the case of an inverted type, the firstelectrode may be a cathode and the second electrode may be an anode.

The organic material layer may include a hole injection layer (120), ahole transport layer (130), an emitting layer (140), an electrontransport layer (150), and an electron injection layer (160).Specifically, a hole injection layer (120), a hole transport layer(130), an emitting layer (140), an electron transport layer (150), andan electron injection layer (160) may be sequentially formed on thefirst electrode (110).

The present invention may further include a light efficiency enhancinglayer formed on one of not in contact with the organic material layeramong one side of the first electrode (110) or of the second electrode(170), and when the light efficiency enhancing layer (180) is formed,the light efficiency of the organic electronic element may be improved.

For example, the light efficiency enhancing layer (180) may be formed onthe second electrode (170), and in the case of a top emission organiclight emitting device, the light efficiency enhancing layer (180) isformed, thereby reducing optical energy loss due to surface plasmonpolaritons (SPPs) in the second electrode (170), and in the case of abottom emission organic light emitting device, the light efficiencyenhancing layer (180) may function as a buffer for the second electrode(170).

A buffer layer (210) or an emitting auxiliary layer (220) may be furtherformed between the hole transport layer (130) and the emitting layer(140), which will be described with reference to FIG. 2.

Referring to FIG. 2, an organic electric device (200) according toanother embodiment of the present invention includes a hole injectionlayer (120), a hole transport layer (130), a buffer layer (210), anemitting auxiliary layer (220), an emitting layer (140), an electrontransport layer (150), an electron injection layer (160), a secondelectrode (170), sequentially formed on the first electrode (110), and alight efficiency enhancing layer (180) formed on the second electrode.

Although not shown in FIG. 2, an electron transport auxiliary layer maybe further formed between the emitting layer (140) and the electrontransport layer (150).

Also, according to another embodiment of the present invention, theorganic material layer may have a plurality of stacks including a holetransport layer, an emitting layer, and an electron transport layer.This will be described with reference to FIG. 3.

Referring to FIG. 3, in the organic electronic element (300) accordingto another embodiment of the present invention, 2 or more sets of stacks(ST1 and ST2) made of a multi-layered organic material layer may beformed between the first electrode (110) and the second electrode (170),and a charge generation layer (CGL) may be formed between the stacks oforganic material layers.

Specifically, the organic electronic element according to an embodimentof the present invention includes a first electrode (110), a first stack(ST1), a charge generation layer (CGL), a second stack (ST2), and asecond electrode. (170) and a light efficiency enhancing layer (180) maybe included.

The first stack (ST1) is an organic material layer formed on the firstelectrode (110) and may include a first hole injection layer (320), afirst hole transport layer (330), a first emitting layer (340), and afirst electron transport layer (350), and the second stack (ST2) mayinclude a second hole injection layer (420), a second hole transportlayer (430), a second emitting layer (440), and a second electrontransport layer (450). As described above, the first stack and thesecond stack may be organic material layers having the same laminatedstructure, but may be organic material layers having different laminatedstructures.

A charge generation layer (CGL) may be formed between the first stack(ST1) and the second stack (ST2). The charge generation layer (CGL) mayinclude a first charge generation layer (360) and a second chargegeneration layer (361). The charge generation layer (CGL) is formedbetween the first emitting layer (340) and the second emitting layer(440) to increase the current efficiency generated in each emittinglayer and smoothly distribute charge.

When a plurality of emitting layers are formed by the multilayer stackstructure method as shown in FIG. 3, an organic electronic element thatemits white light by a mixing effect of light emitted from each emittinglayer can be manufactured, as well as an organic electronic element thatemits light of various colors.

The compounds represented by Formulas 1 and 2 of the present inventionmay be used as a material for a hole injection layer (120, 320, 420), ahole transport layer (130, 330, 430), a buffer layer (210), an emittingauxiliary layer (220), and an electron transport layer (150, 350, 450),the electron injection layer (160), the emitting layer (140, 340, 440),or the light efficiency enhancing layer (180), but preferably, thecompounds represented by Formulas 1 and 2 of the present invention maybe used as a host of the emitting layers (140, 340, 440).

Otherwise, even if the same or similar core is used, the band gap, theelectrical characteristics, the interface characteristics, and the likemay vary depending on which substituent is bonded at which position,therefore the choice of core and the combination of sub-substituentsassociated therewith is also very important, and in particular, when theoptimal combination of energy levels and T1 values and unique propertiesof materials (mobility, interfacial characteristics, etc.) of eachorganic material layer is achieved, a long lifespan and high efficiencycan be achieved at the same time.

The organic electronic element according to an embodiment of the presentinvention may be manufactured using various deposition methods. It canbe manufactured using a vapor deposition method such as PVD or CVD. Forexample, an anode (110) is formed by depositing a metal or a conductivemetal oxide or an alloy thereof on a substrate, and after forming anorganic material layer including the hole injection layer (120), thehole transport layer (130), the emitting layer (140), the electrontransport layer (150) and the electron injection layer (160) thereon,the organic electroluminescent device according to an embodiment of thepresent invention can be manufactured by depositing a material that canbe used as a cathode (170) thereon. Also, an emitting auxiliary layer(220) may be further formed between the hole transport layer (130) andthe emitting layer (140), and an electron transport auxiliary layer (notshown) may be further formed between the emitting layer (140) and theelectron transport layer (150), and as described above, may be formed ina stack structure.

Also, the organic material layer may be manufactured with a smallernumber of layers by using various polymer materials and not by adeposition method, but by a solution process, a solvent process, such asa spin coating process, a nozzle printing process, an inkjet printingprocess, a slot coating process, a dip coating process or a roll-to-rollprocess, doctor blading process, screen printing process, or a thermaltransfer method. Since the organic material layer according to thepresent invention can be formed by various methods, the scope of thepresent invention is not limited by the forming method.

In addition, the organic electric device according to an embodiment ofthe present invention may be selected from the group consisting of anorganic electroluminescent device, an organic solar cell, an organicphotoreceptor, an organic transistor, a monochromatic lighting device,and a quantum dot display device.

Another embodiment of the present invention may include an electronicdevice comprising a display device including the organic electronicelement; and a control unit for driving the display device. At thistime, the electronic device may be a current or future wired/wirelesscommunication terminal, and covers all kinds of electronic devicesincluding a mobile communication terminal such as a cellular phone, apersonal digital assistant (PDA), an electronic dictionary, apoint-to-multipoint (PMP), a remote controller, a navigation unit, agame player, various kinds of TVs, and various kinds of computers.

Hereinafter, an organic electronic element according to an aspect of thepresent invention will be described.

The present invention provides an organic electronic element comprisinga first electrode, a second electrode, and an organic material layerformed between the first electrode and the second electrode, wherein theorganic material layer comprises an emitting layer, wherein the emittinglayer comprises a first host compound represented by Formula 1 and asecond host compound represented by Formula 2 as the phosphorescentemitting layer.

In Formulas 1 and 2, each symbol may be defined as follows.

1) A ring and B ring are each independently a C₆-C₂₀ aryl group; or aC₂-C₆₀ heterocyclic group; provided that at least one of the A ring andB ring is a C₁₀-C₂₀ aryl group, R³ can be substituted in ring A, and R⁴can be substituted in ring B.

2) X¹, X² and X³ are each independently CR or N, provided that at leastone of X¹, X² and X³ are N.

3) R¹, R², R³, R⁴ and R are each the same or different, and eachindependently selected from a group consisting of hydrogen; a C₆-C₆₀aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including atleast one hetero atom of O, N, S, Si or P; a fused ring group of aC₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group;a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group;a C₆-C₃₀ aryloxy group; and -L′—N(R^(a))(R^(b));

When R¹, R², R³, R⁴ and R are an aryl group, it is preferably a C₆-C₃₀aryl group, more preferably an C₆-C₂₄ aryl group, for example, it may bephenylene, biphenyl, naphthalene, terphenyl, and the like.

When R¹, R², R³, R⁴ and R are a heterocyclic group, it is preferably aC₂-C₃₀ heterocyclic group, and more preferably a C₂-C₂₄ heterocyclicgroup, for example, it may be Pyrazine, thiophene, pyridine,pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline,benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran,Benzothienopyrimidine, benzofuropyrimidine, phenothiazine,phenylphenothiazine.

When R¹, R², R³, R⁴ and R are a fused ring group, it is preferably afused ring group of an C₃-C₃₀ aliphatic ring and an C₆-C₃₀ aromaticring, and more preferably a fused ring group of an C₃-C₂₄ aliphatic ringand an C₆-C₂₄ aromatic ring,

When R¹, R², R³, R⁴ and R are an alkyl group, it is preferably a C₁-C₃₀alkyl group, and more preferably a C₁-C₂₄ alkyl group.

When R¹, R², R³, R⁴ and R are an alkoxyl group, it is preferably aC₁-C₂₄ alkoxyl group.

When R¹, R², R³, R⁴ and R are an aryloxy group, it is preferably aC₆-C₂₄ aryloxy group.

4) R^(a) and R^(b) are each independently selected from the groupconsisting of a C₆-C₆₀ aryl group; a fluorenyl group; a fused ring groupof a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₂-C₆₀heterocyclic group including at least one heteroatom of O, N, S, Si orP;

When R^(a) and R^(b) are an aryl group, it is preferably an C₆-C₃₀ arylgroup, more preferably an C₆-C₂₄ aryl group, for example, it may bephenylene, biphenyl, naphthalene, terphenyl, and the like.

When R^(a) and R^(b) are a fused ring group, it is preferably a fusedring group of an C₃-C₃₀ aliphatic ring and an C₆-C₃₀ aromatic ring, andmore preferably a fused ring group of an C₃-C₂₄ aliphatic ring and anC₆-C₂₄ aromatic ring,

When R^(a) and R^(b) are a heterocyclic group, it is preferably a C₂-C₃₀heterocyclic group, and more preferably a C₂-C₂₄ heterocyclic group, forexample, it may be Pyrazine, thiophene, pyridine, pyrimidoindole,5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline,carbazole, dibenzoquinazole, dibenzofuran, Benzothienopyrimidine,benzofuropyrimidine, phenothiazine, phenylphenothiazine.

5) L′, L¹, L², L³, L⁴, L⁵ and L⁶ are each independently selected fromthe group consisting of single bond; a C₆-C₆₀ arylene group; afluorenylene group; a C₂-C₆₀ heterocyclic group including at least oneheteroatom of O, N, S, Si or P;

a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromaticring; a C₂-C₆₀ heterocyclic group; a C₁-C₅₀ alkyl group; a C₂-C₂₀alkenyl group; a C₂-C₂₀ alkynyl group;

wherein in case L′, L¹, L², L³, L⁴, L⁵ and L⁶ are an arylene group, itis preferably an C₆-C₃₀ arylene group, more preferably an C₆-C₂₄ arylenegroup, for example, it may be phenylene, biphenyl, naphthalene,terphenyl, and the like.

when L′, L¹, L², L³, L⁴, L⁵ and L⁶ are a heterocyclic group, it ispreferably a C₂-C₃₀ heterocyclic group, and more preferably a C₂-C₂₄heterocyclic group, for example, it may be Pyrazine, thiophene,pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole,quinazoline, benzoquinazoline, carbazole, dibenzoquinazole,dibenzofuran, Benzothienopyrimidine, benzofuropyrimidine, phenothiazine,phenylphenothiazine.

when L′, L¹, L², L³, L⁴, L⁵ and L⁶ are a fused ring group, it ispreferably a fused ring group of an C₃-C₃₀ aliphatic ring and an C₆-C₃₀aromatic ring, and more preferably a fused ring group of an C₃-C₂₄aliphatic ring and an C₆-C₂₄ aromatic ring, when L′, L¹, L², L³, L⁴, L⁵and L⁶ are an alkyl group, it is preferably a C₁-C₃₀ alkyl group, andmore preferably a C₁-C₂₄ alkyl group.

6) L⁷ is an C₆-C₃₀ arylene group; or fluorenylene group; when L⁷ is anarylene group, it is preferably an C₆-C₃₀ arylene group, more preferablyan C₆-C₂₄ arylene group, for example, it may be phenylene, biphenyl,naphthalene, terphenyl, and the like.

7) Ar¹, Ar², Ar³, Ar⁴, Ar⁵ and Ar⁶ are each independently selected fromthe group consisting of an C₆-C₆₀ aryl group; a C₂-C₆₀ heterocyclicgroup including at least one heteroatom of O, N, S, Si or P; a fluorenylgroup; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic ring; C₁-C₅₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynylgroup; C₁-C₃₀ alkoxyl group; C₆-C₃₀ arylthio group; and C₆-C₃₀ aryloxygroup; however, at least one of Ar⁴, Ar⁵ and Ar⁶ is a substituted orunsubstituted naphthyl group.

When Ar¹, Ar², Ar³, Ar⁴, Ar⁵ and Ar⁶ are an aryl group, it is preferablyan C₆-C₃₀ aryl group, more preferably an C₆-C₂₄ aryl group, for example,it may be phenylene, biphenyl, naphthalene, terphenyl, and the like.

When Ar¹, Ar², Ar³, Ar⁴, Ar⁵ and Ar⁶ are a heterocyclic group, it ispreferably a C₂-C₃₀ heterocyclic group, and more preferably a C₂-C₂₄heterocyclic group, for example, it may be Pyrazine, thiophene,pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole,quinazoline, benzoquinazoline, carbazole, dibenzoquinazole,dibenzofuran, Benzothienopyrimidine, benzofuropyrimidine, phenothiazine,phenylphenothiazine.

when Ar¹, Ar², Ar³, Ar⁴, Ar⁵ and Ar⁶ are a fused ring group, it ispreferably a fused ring group of an C₃-C₃₀ aliphatic ring and an C₆-C₃₀aromatic ring, and more preferably a fused ring group of an C₃-C₂₄aliphatic ring and an C₆-C₂₄ aromatic ring,

when Ar¹, Ar², Ar³, Ar⁴, Ar⁵ and Ar⁶ are an alkyl group, it ispreferably a C₁-C₃₀ alkyl group, and more preferably a C₁-C₂₄ alkylgroup.

when Ar¹, Ar², Ar³, Ar⁴, Ar⁵ and Ar⁶ are an alkoxyl group, it ispreferably a C₁-C₂₄ alkoxyl group.

when Ar¹, Ar², Ar³, Ar⁴, Ar⁵ and Ar⁶ are an arylthio group, it ispreferably a C₁-024 arythio group.

when Ar¹, Ar², Ar³, Ar⁴, Ar⁵ and Ar⁶ are an aryloxy group, it ispreferably a C₁-C₂₄ aryloxy group.

8) X is O or S.

9) a is an integer of 0 to 3, b is an integer of 0 to 4.

10) wherein, the aryl group, arylene group, heterocyclic group,fluorenyl group, fluorenylene group, aliphatic ring, fused ring group,alkyl group, alkenyl group, alkoxy group, aryloxy group and arylthiogroup may be substituted with one or more substituents selected from thegroup consisting of deuterium; halogen; silane group; siloxane group;boron group; germanium group; cyano group; nitro group; C₁-C₂₀ alkylthiogroup; C₁-C₂₀ alkoxy group; C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group;C₂-C₂₀ alkynyl group; C₆-C₂₀ aryl group; C₆-C₂₀ aryl group substitutedwith deuterium; a fluorenyl group; C₂-C₂₀ heterocyclic group; C₃-C₂₀cycloalkyl group; C₇-C₂₀ arylalkyl group; C₈-C₂₀ arylalkenyl group; and-L′—N(R^(a))(R^(b)); the substituents may be bonded to each other toform a saturated or unsaturated ring, wherein the term ‘ring’ means aC₃-C₆₀ aliphatic ring or a C₆-C₆₀ aromatic ring or a C₂-C₆₀ heterocyclicgroup or a fused ring formed by the combination thereof.

Also, the present invention provides an organic electronic elementwherein at least one of ring A and ring B of Formula 1 is represented byany one of Formulas a-1 to a-6.

{In Formulas a-1 to a-6,

-   -   1) Z¹ to Z⁴⁴ are each independently CR^(a) or N,

Z¹ to Z⁴⁴ bonded to L³ are carbon (C),

-   -   2) R^(a) is the same as the definition of R¹ in Formula 1,

* indicates the position to be condensed.}

Also, the present invention provides an organic electronic elementincluding a compound wherein L¹, L³, L⁴, L⁵ and L⁶ are represented byany one of the following Formulas b-1 to b-16.

In Formulas b-1 to b-16, each symbol may be defined as follows.

-   -   1) Y is N-L⁸—Ar⁷, O, S or CR′R″,    -   2) L⁸ is the same as the definition of L¹ in Formula 1,    -   3) Ar⁷ is the same as the definition of Ar¹ in Formula 1,    -   4) R′ and R″ are the same as definition of R¹ in Formula 1, or        may be bonded to each other to form a ring,    -   5) a′, c′, d′ and e′ are each independently an integer of 0 to        4, and b′ is an integer of 0 to 6, f′ and g′ are each        independently an integer of 0 to 3, h′ is an integer of 0 to 2,    -   6) R⁵, R⁶ and R⁷ are each independently selected from the group        consisting of hydrogen; deuterium; tritium; halogen; cyano        group; nitro group; a C₆-C₆₀ aryl group; a fluorenyl group; a        C₂-C₆₀ heterocyclic group including at least one heteroatom of        O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring        and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀        alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a        C₆-C₃₀ aryloxy group; and -L^(a)-N(R^(c))(R^(d)); or in case a′,        b′, c′, d′, e′, f′, g′ and h′ are 2 or more, R⁵, R⁶ and R⁷ are        in plural being the same or different, and a plurality of R⁵ or        a plurality of R⁶ or a plurality of R⁷ or adjacent R⁵ and R⁶, or        adjacent R⁶ and R⁷ may be bonded to each other to form an        aromatic or a heteroaromatic ring,

When R⁵, R⁶ and R⁷ are an aryl group, it is preferably an C₆-C₃₀ arylgroup, more preferably an C₆-C₂₄ aryl group, for example, it may bephenylene, biphenyl, naphthalene, terphenyl, and the like.

When R⁵, R⁶ and R⁷ are a heterocyclic group, it is preferably a C₂-C₃₀heterocyclic group, and more preferably a C₂-C₂₄ heterocyclic group, forexample, it may be Pyrazine, thiophene, pyridine, pyrimidoindole,5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline,carbazole, dibenzoquinazole, dibenzofuran, Benzothienopyrimidine,benzofuropyrimidine, phenothiazine, phenylphenothiazine.

when R⁵, R⁶ and R⁷ are a fused ring group, it is preferably a fused ringgroup of an C₃-C₃₀ aliphatic ring and an C₆-C₃₀ aromatic ring, and morepreferably a fused ring group of an C₃-C₂₄ aliphatic ring and an C₆-C₂₄aromatic ring,

when R⁵, R⁶ and R⁷ are an alkyl group, it is preferably a C₁-C₃₀ alkylgroup, and more preferably a C₁-C₂₄ alkyl group.

when R⁵, R⁶ and R⁷ are an alkoxyl group, it is preferably a C₁-C₂₄alkoxyl group.

when R⁵, R⁶ and R⁷ are an aryloxy group, it is preferably a C₁-C₂₄aryloxy group.

7) L^(a) is the same as the definition of L¹ in Formula 1,

8) R^(c) and R^(d) are the same as the definition of R^(a) in Formula 1,

9) Y¹, Y² and Y³ are each independently CR^(e) or N, provided that atleast one of Y¹, Y² and Y³ is N,

10) R^(e) is selected from the group consisting of hydrogen; deuterium;tritium; halogen; cyano group; nitro group; a C₆-C₆₀ aryl group; afluorenyl group; a C₂-C₆₀ heterocyclic group including at least oneheteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphaticring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenylgroup; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxygroup;

When R^(e) are an aryl group, it is preferably an C₆-C₃₀ aryl group,more preferably an C₆-C₂₄ aryl group, for example, it may be phenylene,biphenyl, naphthalene, terphenyl, and the like.

When R^(e) are a heterocyclic group, it is preferably a C₂-C₃₀heterocyclic group, and more preferably a C₂-C₂₄ heterocyclic group, forexample, it may be Pyrazine, thiophene, pyridine, pyrimidoindole,5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline,carbazole, dibenzoquinazole, dibenzofuran, Benzothienopyrimidine,benzofuropyrimidine, phenothiazine, phenylphenothiazine.

when R^(e) are a fused ring group, it is preferably a fused ring groupof an C₃-C₃₀ aliphatic ring and an C₆-C₃₀ aromatic ring, and morepreferably a fused ring group of an C₃-C₂₄ aliphatic ring and an C₆-C₂₄aromatic ring,

when R^(e) are an alkyl group, it is preferably a C₁-C₃₀ alkyl group,and more preferably a C₁-C₂₄ alkyl group.

when R^(e) are an alkoxyl group, it is preferably a C₁-C₂₄ alkoxylgroup.

when R^(e) are an aryloxy group, it is preferably a C₁-C₂₄ aryloxygroup.

11) Adjacent R⁵ and R^(e) may be bonded to each other to form anaromatic ring or a heteroaromatic ring,

12)

indicates the position to be condensed.

The first host compound represented by Formula 1 is represented by anyone of Formulas 1-1 to 1-8.

{In Formulas 1-1 to 1-8,

1) X, Ar¹, Ar², Ar³, L¹, L², L³, L⁷, R¹, R², R³, R⁴, a and b are thesame as defined in Formula 1,

2) e is an integer of 0 to 4, and f is an integer of 0 to 5, g is aninteger of 0 to 6, h is an integer of 0 to 3, i is an integer of 0 to 7,j is an integer of 0 to 8.}

Specifically, the compound represented by Formula 1 may be any one ofthe following compounds.

Also, at least one of Ar⁴ to Ar⁶ in Formula 2 is represented by Formulac-1 to Formula c-6

{In Formula c-1 to Formula c-6,

1) R⁸ and R^(a1) to R^(a14) are each independently hydrogen; a C₁-C₂₀alkyl group; a C₆-C₂₀ aryl group; a C₆-C₂₀ aryl group substituted bydeuterium; a fluorenyl group; a C₂-C₂₀ heterocyclic group;

2) c is an integer of 0 to 3, d is an integer of 0 to 4.}

Also, the second host compound represented by Formula 2 is representedby any one of Formulas 2-1 to 2-4.

{In Formula 2-1 to Formula 2-4,

1) Ar⁵, Ar⁶, X¹, X², X³, L⁴, L⁵ and L⁶ are the same as defined inFormula 2,

2) R⁸ is hydrogen; a C₁-C₂₀ alkyl group; a C₆-C₂₀ aryl group; a C₆-C₂₀aryl group substituted by deuterium; a fluorenyl group; a C₂-C₆₀heterocyclic group;

2) k is an integer of 0 to 7.}

The second host compound represented by Formula 2 is represented by anyone of the following Formulas 2-5 to 2-8.

{In Formulas 2-5 to 2-8,

1) Ar⁵, Ar⁶, L⁴, L⁵ and L⁶ are the same as defined in Formula 2,

2) R⁸ is hydrogen; a C₁-C₂₀ alkyl group; a C₆-C₂₀ aryl group; a C₆-C₂₀aryl group substituted by deuterium; a fluorenyl group; a C₂-C₆₀heterocyclic group;

3) R⁹, R¹⁰, R¹¹, R¹² and R¹³ are the same as definition of R¹ in Formula1,

4) Y² is CR¹⁴R¹⁵, N—Ar⁷, O or S,

5) wherein R¹⁴ and R¹⁵ are the same as definition of R¹ in Formula 1,

6) Ar⁷ is the same as definition of Ar¹ in Formula 1,

7) k and 1 are each independently an integer of 0 to 7, m and o are eachindependently an integer of 0 to 4, n is an integer of 0 to 5, and p isan integer of 0 to 3.}

Specifically, the compound represented by Formula 2 may be any one ofthe following compounds.

The present invention may further include a light efficiency enhancinglayer formed on at least one surface of the first electrode and thesecond electrode opposite to the organic material layer.

Also, the organic material layer may include 2 or more stacks includinga hole transport layer, an emitting layer, and an electron transportlayer sequentially formed on the anode, and the organic material layermay further include a charge generation layer formed between the 2 ormore stacks.

In another aspect, the present invention provides an electronic devicecomprising a display device including the organic electronic element;and a control unit for driving the display device; here, the organicelectronic element is at least one of an OLED, an organic solar cell, anorganic photo conductor, an organic transistor and an element formonochromic or white illumination.

Hereinafter, Synthesis Examples of the compound represented by Formulaaccording to the present invention and preparation examples of theorganic electronic element according to the present invention will bedescribed in detail by way of example, but are not limited to thefollowing examples of the invention.

Synthesis Example 1

The compound represented by Formula 1 according to the present invention(final product 1) (disclosed in Korean Patent Registration Nos.10-2018682, 10-2018683 (registration notice dated Sep. 4, 2019) of theapplicant) is synthesized by reacting Sub 1 and Sub 2 as shown in Scheme1, but is not limited thereto.

I. Synthesis of Sub 1

Sub 1 of Reaction Scheme 1 may be synthesized by Reaction Scheme 2, butis not limited thereto.

1. Synthesis Example of Sub 1-P-2

Aniline (50 g, 536.9 mmol), 3-bromonaphtho[2,3-b]benzofuran (158.9 g,536.9 mmol), Pd₂(dba)₃ (14.75 g, 16.1 mmol), P(t-Bu)₃ (6.52 g, 32.2mmol), NaOt-Bu (103.2 g, 1073.8 mmol), toluene (2,684 mL) were added ina round bottom flask, followed by reaction at 100° C. When the reactionwas completed, the resulting compound was extracted with CH₂Cl₂ andwater, and the organic layer was dried over MgSO₄, concentrated, and theresulting compound was recrystallized with a silica gel column to obtain129.5 g of a product. (Yield: 78%)

2. Synthesis Example of Sub 1-P-45

Aniline (10 g, 107.4 mmol),2-(6-chloronaphthalen-2-yl)benzo[b]naphtho[2,3-d]thiophene (42.4 g,107.4 mmol), Pd₂(dba)₃ (3 g, 3.2 mmol), P(t-Bu)₃ (1.4 g, 6.4 mmol),NaOt-Bu (20.6 g, 214.8 mmol), toluene (550 mL) were added in a roundbottom flask, followed by reaction at 100° C. When the reaction wascompleted, the resulting compound was extracted with CH₂Cl₂ and water,and the organic layer was dried over MgSO₄, concentrated, and theresulting compound was recrystallized with a silica gel column to obtain34.4 g of a product. (Yield: 71%)

The compound belonging to Sub 1 may be a compound as follows, but is notlimited thereto, and Table 1 shows FD-MS (Field Desorption-MassSpectrometry) values of some compounds belonging to Sub 1.

TABLE 1 compound FD-MS compound FD-MS Sub1-P-1 m/z = 309.12(C₂₂H₁₅NO =309.37) Sub1-P-2 m/z = 309.12(C₂₂H₁₅NO = 309.37) Sub1-P-3 m/z =309.12(C₂₂H₁₅NO = 309.37) Sub1-P-4 m/z = 309.12(C₂₂H₁₅NO = 309.37)Sub1-P-5 m/z = 309.12(C₂₂H₁₅NO = 309.37) Sub1-P-6 m/z = 309.12(C₂₂H₁₅NO= 309.37) Sub1-P-7 m/z = 309.12(C₂₂H₁₅NO = 309.37) Sub1-P-8 m/z =309.12(C₂₂H₁₅NO = 309.37) Sub1-P-9 m/z = 309.12(C₂₂H₁₅NO = 309.37)Sub1-P-10 m/z = 309.12(C₂₂H₁₅NO = 309.37) Sub1-P-11 m/z =309.12(C₂₂H₁₅NO = 309.37) Sub1-P-12 m/z = 309.12(C₂₂H₁₅NO = 309.37)Sub1-P-13 m/z = 309.12(C₂₂H₁₅NO = 309.37) Sub1-P-14 m/z =309.12(C₂₂H₁₅NO = 309.37) Sub1-P-15 m/z = 309.12(C₂₂H₁₅NO = 309.37)Sub1-P-16 m/z = 309.12(C₂₂H₁₅NO = 309.37) Sub1-P-17 m/z =309.12(C₂₂H₁₅NO = 309.37) Sub1-P-18 m/z = 309.12(C₂₂H₁₅NO = 309.37)Sub1-P-19 m/z = 309.12(C₂₂H₁₅NO = 309.37) Sub1-P-20 m/z =309.12(C₂₂H₁₅NO = 309.37) Sub1-P-21 m/z = 309.12(C₂₂H₁₅NO = 309.37)Sub1-P-22 m/z = 309.12(C₂₂H₁₅NO = 309.37) Sub1-P-23 m/z =309.12(C₂₂H₁₅NO = 309.37) Sub1-P-24 m/z = 309.12(C₂₂H₁₅NO = 309.37)Sub1-P-25 m/z = 309.12(C₂₂H₁₅NO = 309.37) Sub1-P-26 m/z =309.12(C₂₂H₁₅NO = 309.37) Sub1-P-27 m/z = 309.12(C₂₂H₁₅NO = 309.37)Sub1-P-28 m/z = 309.12(C₂₂H₁₅NO = 309.37) Sub1-P-29 m/z =309.12(C₂₂H₁₅NO = 309.37) Sub1-P-30 m/z = 309.12(C₂₂H₁₅NO = 309.37)Sub1-P-31 m/z = 325.09(C₂₂H₁₅NS = 325.43) Sub1-P-32 m/z =325.09(C₂₂H₁₅NS = 325.43) Sub1-P-33 m/z = 325.09(C₂₂H₁₅NS = 325.43)Sub1-P-34 m/z = 325.09(C₂₂H₁₅NS = 325.43) Sub1-P-35 m/z =325.09(C₂₂H₁₅NS = 325.43) Sub1-P-36 m/z = 325.09(C₂₂H₁₅NS = 325.43)Sub1-P-37 m/z = 325.09(C₂₂H₁₅NS = 325.43) Sub1-P-38 m/z =325.09(C₂₂H₁₅NS = 325.43) Sub1-P-39 m/z = 359.13(C₂₆H₁₇NO = 359.43)Sub1-P-40 m/z = 325.09(C₂₂H₁₅NS = 325.43) Sub1-P-41 m/z =401.12(C₂₈H₁₉NS = 401.53) Sub1-P-42 m/z = 385.15(C₂₈H₁₉NO = 385.47)Sub1-P-43 m/z = 385.15(C₂₈H₁₉NO = 385.47) Sub1-P-44 m/z =385.15(C₂₈H₁₉NO = 385.47) Sub1-P-45 m/z = 451.14(C₃₂H₂₁NS = 451.59)

II. Synthesis of Sub 2

Sub 2 of Reaction Scheme 1 may be synthesized by the reaction path ofScheme 3, but is not limited thereto.

1. Synthesis Example of Sub2-P-1

1-chloro-4-iodobenzene (25 g, 104.8 mmol),N,9-diphenyl-9H-carbazol-2-amine (35 g, 104.8 mmol), Pd₂(dba)₃ (7.4 g,8.1 mmol), P(t-Bu)₃ (3.3 g, 16.2 mmol), NaOt-Bu (51.6 g, 536.9 mmol),toluene (1,000 mL) were added in a round bottom flask, followed byreaction at 100° C. When the reaction was completed, the resultingcompound was extracted with CH₂Cl₂ and water, and the organic layer wasdried over MgSO₄, concentrated, and the resulting compound wasrecrystallized with a silica gel column to obtain 38.7 g of a product.(Yield: 84%)

2. Synthesis Example of Sub2-P-17

3-chloro-4′-iodo-1,1′-biphenyl (32.9 g, 104.8 mmol),N,9-diphenyl-9H-carbazol-2-amine (35 g, 104.8 mmol), Pd₂(dba)₃ (7.4 g,8.1 mmol), P(t-Bu)₃ (3.3 g, 16.2 mmol), NaOt-Bu (51.6 g, 536.9 mmol),toluene (1,000 mL) were added in a round bottom flask, followed byreaction at 100° C. When the reaction was completed, the resultingcompound was extracted with CH₂Cl₂ and water, and the organic layer wasdried over MgSO₄, concentrated, and the resulting compound wasrecrystallized with a silica gel column to obtain 44.2 g of a product.(Yield: 81%)

Compounds belonging to Sub 2 may be compounds as follows, but are notlimited thereto, and Table 2 shows FD-MS (Field Desorption-MassSpectrometry) values of some compounds belonging to Sub 2.

TABLE 2 compound FD-MS compound FD-MS Sub2-P-1 m/z = 444.14(C₃₀H₂₁ClN₂ =444.96) Sub2-P-2 m/z = 444.14(C₃₀H₂₁ClN₂ = 444.96) Sub2-P-3 m/z =444.14(C₃₀H₂₁ClN₂ = 444.96) Sub2-P-4 m/z = 520.17(C₃₆H₂₅ClN₂ = 521.06)Sub2-P-5 m/z = 520.17(C₃₆H₂₅ClN₂ = 521.06) Sub2-P-6 m/z =520.17(C₃₆H₂₅ClN₂ = 521.06) Sub2-P-7 m/z = 499.19(C₃₄H₁₈D₅ClN₂ = 500.05)Sub2-P-8 m/z = 520.17(C₃₆H₂₅ClN₂ = 521.06) Sub2-P-9 m/z =480.12(C₃₀H₁₉ClF₂N₂ = 480.94) Sub2-P-10 m/z = 494.15(C₃₄H₂₃ClN₂ =495.02) Sub2-P-11 m/z = 520.17(C₃₆H₂₅ClN₂ = 521.06) Sub2-P-12 m/z =560.2(C₃₉H₂₉ClN₂ = 561.13) Sub2-P-13 m/z = 494.15(C₃₄H₂₃ClN₂ = 495.02)Sub2-P-14 m/z = 494.15(C₃₄H₂₃ClN₂ = 495.02) Sub2-P-15 m/z =494.15(C₃₄H₂₃ClN₂ = 495.02) Sub2-P-16 m/z = 520.17(C₃₆H₂₅ClN₂ = 521.06)Sub2-P-17 m/z = 520.17(C₃₆H₂₅ClN₂ = 521.06) Sub2-P-18 m/z =520.17(C₃₆H₂₅ClN₂ = 521.06) Sub2-P-19 m/z = 520.17(C₃₆H₂₅ClN₂ = 521.06)Sub2-P-20 m/z = 520.17(C₃₆H₂₅ClN₂ = 521.06) Sub2-P-21 m/z =534.15(C₃₆H₂₃ClN₂O = 535.04) Sub2-P-22 m/z = 534.15(C₃₆H₂₃ClN₂O =535.04) Sub2-P-23 m/z = 550.13(C₃₆H₂₃ClN₂S = 551.1) Sub2-P-24 m/z =550.13(C₃₆H₂₃ClN₂S = 551.1)

III. Synthesis of Final Product 1

After dissolving Sub 1 (1 eq.) with Toluene in a round bottom flask, Sub2 (1 eq.), Pd₂(dba)₃ (0.05 eq.), (t-Bu)₃P (0.1 eq.), and NaOt-Bu (3 eq.)were stirred at 100° C. When the reaction was completed, the resultingcompound was extracted with CH₂Cl₂ and water, and the organic layer wasdried over MgSO₄ and concentrated, and the resulting compound wasrecrystallized with a silica gel column to obtain Final product 1.

1. Synthesis Example of P-1

After dissolving Sub 1-1 (13.7 g, 20.5 mmol) with Toluene (180 in around bottom flask, Sub 2-1 (3.48 g, 20.5 mmol), Pd₂(dba)₃ (0.56 g, 0.62mmol), P(t-Bu)₃ (4.16 g, 20.5 mmol), NaOt-Bu (3.95 g, 41.1 mmol) wereadded and stirred at 120° C. When the reaction was completed, theresulting compound was extracted with CH₂Cl₂ and water, and the organiclayer was dried over MgSO₄ and concentrated, and the resulting compoundwas recrystallized with a silica gel column to obtain P-1 (6 g, yield:84%)

2. Synthesis Example of P-13

Sub1-P-2 (3.1 g, 10 mmol) and Sub2-P-7 (5 g, 10 mmol) were used toobtain a product (6.5 g, 85%) using the synthesis method of P-1.

3. Synthesis Example of P-43

Sub1-P-32 (3.3 g, 10 mmol) and Sub2-P-9 (4.8 g, 10 mmol) were used toobtain a product (5.9 g, 76%) using the synthesis method of P-1.

4. Synthesis Example of P-61

Sub1-P-14 (3.1 g, 10 mmol) and Sub2-P-2 (4.4 g, 10 mmol) were used toobtain a product (5.1 g, 71%) using the synthesis method of P-1.

5. Synthesis Example of P-97

Sub1-P-35 (3.3 g, 10 mmol) and Sub2-P-2 (4.4 g, 10 mmol) were used toobtain a product (5.4 g, 74%) using the synthesis method of P-1.

6. Synthesis Example of P-109

Sub1-P-26 (3.1 g, 10 mmol) and Sub2-P-2 (4.4 g, 10 mmol) were used toobtain a product (4.8 g, 67%) using the synthesis method of P-1.

7. Synthesis Example of P-123

Sub1-P-27 (3.1 g, 10 mmol) and Sub2-P-3 (4.4 g, 10 mmol) were used toobtain a product (4 g, 56%) using the synthesis method of P-1.

Meanwhile, FD-MS values of the compounds P-1 to P-128 of the presentinvention prepared according to the synthesis example as described aboveare shown in Table 3.

TABLE 3 compound FD-MS compound FD-MS P-1 m/z = 717.28(C₅₂H₃₅N₃O =717.87) P-2 m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-3 m/z = 717.28(C₅₂H₃₅N₃O= 717.87) P-4 m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-5 m/z =717.28(C₅₂H₃₅N₃O = 717.87) P-6 m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-7 m/z= 717.28(C₅₂H₃₅N₃O = 717.87) P-8 m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-9m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-10 m/z = 717.28(C₅₂H₃₅N₃O = 717.87)P-11 m/z = 793.31(C₅₆H₃₉N₃O = 793.97) P-12 m/z = 793.31(C₅₆H₃₉N₃O =793.97) P-13 m/z = 772.33(C₅₆H₃₂D₅N₃O = 772.96) P-14 m/z =767.29(C₅₆H₃₇N₃O = 767.93) P-15 m/z = 807.29(C₅₈H₃₇N₃O₂ = 807.95) P-16m/z = 823.27(C₅₈H₃₇N₃OS = 824.01) P-17 m/z = 833.34(C₆₁H₄₃N₃O = 834.04)P-18 m/z = 882.34(C₆₄H₄₂N₄O = 883.07) P-19 m/z = 767.29(C₅₆H₃₇N₃O =767.93) P-20 m/z = 869.34(C₆₄H₄₃N₃O = 870.07) P-21 m/z =717.28(C₅₂H₃₅N₃O = 717.87) P-22 m/z = 733.26(C₅₂H₃₅N₃S = 733.93) P-23m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-24 m/z = 717.28(C₅₂H₃₅N₃O = 717.87)P-25 m/z = 733.26(C₅₂H₃₅N₃S = 733.93) P-26 m/z = 717.28(C₅₂H₃₅N₃O =717.87) P-27 m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-28 m/z =717.28(C₅₂H₃₅N₃O = 717.87) P-29 m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-30m/z = 733.26(C₅₂H₃₅N₃S = 733.93) P-31 m/z = 717.28(C₅₂H₃₅N₃O = 717.87)P-32 m/z = 733.26(C₅₂H₃₅N₃S = 733.93) P-33 m/z = 717.28(C₅₂H₃₅N₃O =717.87) P-34 m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-35 m/z =733.26(C₅₂H₃₅N₃S = 733.93) P-36 m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-37m/z = 793.31(C₅₈H₃₉N₃O = 793.97) P-38 m/z = 793.31(C₅₈H₃₉N₃O = 793.97)P-39 m/z = 809.29(C₅₈H₃₉N₃S = 810.03) P-40 m/z = 893.34(C₆₆H₄₃N₃O =894.09) P-41 m/z = 733.26(C₅₂H₃₅N₃S = 733.93) P-42 m/z =733.26(C₅₂H₃₅N₃S = 733.93) P-43 m/z = 769.24(C₅₂H₃₃F₂N₃S = 769.91) P-44m/z = 733.26(C₅₂H₃₅N₃S = 733.93) P-45 m/z = 733.26(C₅₂H₃₅N₃S = 733.93)P-46 m/z = 783.27(C₅₆H₃₇N₃S = 783.99) P-47 m/z = 783.27(C₅₆H₃₇N₃S =783.99) P-48 m/z = 733.26(C₅₂H₃₅N₃S = 733.93) P-49 m/z =733.26(C₅₂H₃₅N₃S = 733.93) P-50 m/z = 733.26(C₅₂H₃₅N₃S = 733.93) P-51m/z = 809.29(C₅₈H₃₉N₃S = 810.03) P-52 m/z = 859.3(C₆₂H₄₁N₃S = 860.09)P-53 m/z = 859.3(C₆₂H₄₁N₃S = 860.09) P-54 m/z = 858.28(C₆₁H₃₈N₄S =859.06) P-55 m/z = 973.35(C₇₁H₄₇N₃S = 974.24) P-56 m/z = 859.3(C₆₂H₄₁N₃S= 860.09) P-57 m/z = 857.29(C₆₂H₃₉N₃S = 858.08) P-58 m/z =885.32(C₆₄H₄₃N₃S = 886.13) P-59 m/z = 809.29(C₅₈H₃₉N₃S = 810.03) P-60m/z = 809.29(C₅₈H₃₉N₃S = 810.03) P-61 m/z = 717.28(C₅₂H₃₅N₃O = 717.87)P-62 m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-63 m/z = 717.28(C₅₂H₃₅N₃O =717.87) P-64 m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-65 m/z =717.28(C₅₂H₃₅N₃O = 717.87) P-66 m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-67m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-68 m/z = 717.28(C₅₂H₃₅N₃O = 717.87)P-69 m/z = 745.31(C₅₄H₃₉N₃O = 745.93) P-70 m/z = 717.28(C₅₂H₃₅N₃O =717.87) P-71 m/z = 1047.38(C₇₇H₄₉N₃O₂ = 1048.26) P-72 m/z =807.29(C₅₈H₃₇N₃O₂ = 807.95) P-73 m/z = 767.29(C₅₆H₃₇N₃O = 767.93) P-74m/z = 767.29(C₅₆H₃₇N₃O = 767.93) P-75 m/z = 833.34(C₆₁H₄₃N₃O = 834.04)P-76 m/z = 807.29(C₅₈H₃₇N₃O₂ = 807.95) P-77 m/z = 767.29(C₅₆H₃₇N₃O =767.93) P-78 m/z = 843.32(C₆₂H₄₁N₃O = 844.03) P-79 m/z =882.34(C₆₄H₄₂N₄O = 883.07) P-80 m/z = 793.31(C₅₈H₃₉N₃O = 793.97) P-81m/z = 793.31(C₅₈H₃₉N₃O = 793.97) P-82 m/z = 717.28(C₅₂H₃₅N₃O = 717.87)P-83 m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-84 m/z = 717.28(C₅₂H₃₅N₃O =717.87) P-85 m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-86 m/z =717.28(C₅₂H₃₅N₃O = 717.87) P-87 m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-88m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-89 m/z = 717.28(C₅₂H₃₅N₃O = 717.87)P-90 m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-91 m/z = 717.28(C₅₂H₃₅N₃O =717.87) P-92 m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-93 m/z =733.26(C₅₂H₃₅N₃S = 733.93) P-94 m/z = 733.26(C₅₂H₃₅N₃S = 733.93) P-95m/z = 733.26(C₅₂H₃₅N₃S = 733.93) P-96 m/z = 867.36(C₆₂H₄₉N₃S = 868.16)P-97 m/z = 733.26(C₅₂H₃₅N₃S = 733.93) P-98 m/z = 733.26(C₅₂H₃₅N₃S =733.93) P-99 m/z = 733.26(C₅₂H₃₅N₃S = 733.93) P-100 m/z =733.26(C₅₂H₃₅N₃S = 733.93) P-101 m/z = 793.31(C₅₈H₃₉N₃O = 793.97) P-102m/z = 793.31(C₅₈H₃₉N₃O = 793.97) P-103 m/z = 793.31(C₅₈H₃₉N₃O = 793.97)P-104 m/z = 859.3(C₆₂H₄₁N₃S = 860.09) P-105 m/z = 733.26(C₅₂H₃₅N₃S =733.93) P-106 m/z = 733.26(C₅₂H₃₅N₃S = 733.93) P-107 m/z =767.29(C₅₆H₃₇N₃O = 767.93) P-108 m/z = 733.26(C₅₂H₃₅N₃S = 733.93) P-109m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-110 m/z = 733.26(C₅₂H₃₅N₃S = 733.93)P-111 m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-112 m/z = 733.26(C₅₂H₃₅N₃S =733.93) P-113 m/z = 793.31(C₅₈H₃₉N₃O = 793.97) P-114 m/z =793.31(C₅₈H₃₉N₃O = 793.97) P-115 m/z = 793.31(C₅₈H₃₉N₃O = 793.97) P-116m/z = 843.32(C₆₂H₄₁N₃O = 844.03) P-117 m/z = 793.31(C₅₈H₃₉N₃O = 793.97)P-118 m/z = 733.26(C₅₂H₃₅N₃S = 733.93) P-119 m/z = 717.28(C₅₂H₃₅N₃O =717.87) P-120 m/z = 733.26(C₅₂H₃₅N₃S = 733.93) P-121 m/z =767.29(C₅₆H₃₇N₃O = 767.93) P-122 m/z = 783.27(C₅₆H₃₇N₃S = 783.99) P-123m/z = 717.28(C₅₂H₃₅N₃O = 717.87) P-124 m/z = 783.27(C₅₆H₃₇N₃S = 783.99)P-125 m/z = 793.31(C₅₈H₃₉N₃O = 793.97) P-126 m/z = 793.31(C₅₈H₃₉N₃O =793.97) P-127 m/z = 793.31(C₅₈H₃₉N₃O = 793.97) P-128 m/z =793.31(C₅₈H₃₉N₃O = 793.97)

Synthesis Example 2

The compound (final product 2) represented by Formula 2 according to thepresent invention may be prepared as shown in Scheme 4, but is notlimited thereto.

<Reaction Scheme 4> (Hal⁴ is I, Br, or Cl.)

IV. Synthesis of Final Product 2 1. Synthesis Example of N-1

After placing 2-chloro-4,6-diphenyl-1,3,5-triazine (8 g, 30 mmol) and(3-phenylnaphthalen-2-yl)boronic acid (8.2 g, 33 mmol), K₂CO₃ (12.4 g,90 mmol), Pd(PPh₃)₄ (1.7 g, 1.5 mmol) in a round bottom flask, THF andwater were added to dissolve, and then refluxed at 80° C. for 12 hours.When the reaction was completed, the temperature of the reaction productwas cooled to room temperature, extracted with CH₂Cl₂, and washed withwater. The organic layer was dried over MgSO₄, concentrated, and theresulting organic material was separated using a silica gel column toobtain the desired product (9.54 g, 73%).

2. Synthesis Example of N-19

2,4-di([1,1′-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (12.6 g, 30 mmol)and (5-phenylnaphthalen-2-yl)boronic acid (8.2 g, 33 mmol) were used toobtain a product (15.5 g, 88%) using the synthesis method of N-1.

3. Synthesis Example of N-33

2-chloro-4,6-diphenyl-1,3,5-triazine (8 g, 30 mmol) and[2,2′-binaphthalen]-1-ylboronic acid (9.8 g, 33 mmol) were used toobtain a product (9.8 g, 67%) using the synthesis method of N-1.

4. Synthesis Example of N-53

(1) Synthesis of N-53-1

2,4-dichloro-6-phenyl-1,3,5-triazine (6.8 g, 30 mmol) andnaphthalen-2-ylboronic acid (5.1 g, 30 mmol) were used to obtain aproduct (6.7 g, 70%) using the synthesis method of N-1.

(2) Synthesis of N-53

2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (9.5 g, 30 mmol)and (7-phenylnaphthalen-2-yl)boronic acid (8.2 g, 33 mmol) were used toobtain a product (12.4 g, 85%) using the synthesis method of N-1.

5. Synthesis Example of N-87

2-chloro-4,6-di(naphthalen-2-yl)-1,3,5-triazine (11 g, 30 mmol) and[2,2′-binaphthalen]-6-ylboronic acid (9.8 g, 33 mmol) were used toobtain a product (14.8 g, 84%) using the synthesis method of N-1.

6. Synthesis Example of N-113

2-chloro-4-(naphthalen-2-yl)-6-(naphtho[2,3-b]benzofuran-1-yl)-1,3,5-triazine(13.7 g, 30 mmol) and (7-phenylnaphthalen-2-yl)boronic acid (8.2 g, 33mmol) were used to obtain a product (14.5 g, 77%) using the synthesismethod of N-1.

7. Synthesis Example of N-115

2,4,6-trichloro-1,3,5-triazine (5.5 g, 30 mmol) and(6-phenylnaphthalen-2-yl)boronic acid (23 g, 93 mmol) were used toobtain a product (15 g, 73%) using the synthesis method of N-1.

8. Synthesis Example of N-165

2-chloro-4,6-di(naphthalen-2-yl)-1,3,5-triazine (11 g, 30 mmol) and[1,1′-biphenyl]-4-ylboronic acid (5.9 g, 30 mmol) were used to obtain aproduct (11.9 g, 82%) using the synthesis method of N-1.

9. Synthesis Example of N-177

2-([1,1′-biphenyl]-4-yl)-4,6-dichloro-1,3,5-triazine (9 g, 30 mmol) and(4-(naphthalen-1-yl)phenyl)boronic acid (15.4 g, 62 mmol) were used toobtain a product (12.8 g, 67%) using the synthesis method of N-1.

Meanwhile, FD-MS values of compounds N-1 to N-148 of the presentinvention prepared according to the synthesis example as described aboveare shown in Table 4.

TABLE 4 compound FD-MS compound FD-MS N-1 m/z = 435.17(C₃₁H₂₁N₃ =435.53) N-2 m/z = 435.17(C₃₁H₂₁N₃ = 435.53) N-3 m/z = 435.17(C₃₁H₂₁N₃ =435.53) N-4 m/z = 435.17(C₃₁H₂₁N₃ = 435.53) N-5 m/z = 435.17(C₃₁H₂₁N₃ =435.53) N-6 m/z = 435.17(C₃₁H₂₁N₃ = 435.53) N-7 m/z = 435.17(C₃₁H₂₁N₃ =435.53) N-8 m/z = 434.18(C₃₂H₂₂N₂ = 434.54) N-9 m/z = 511.2(C₃₇H₂₅N₃ =511.63) N-10 m/z = 611.24(C₄₅H₂₉N₃ = 611.75) N-11 m/z = 485.19(C₃₅H₂₃N₃= 485.59) N-12 m/z = 511.2(C₃₇H₂₅N₃ = 511.63) N-13 m/z = 511.2(C₃₇H₂₅N₃= 511.63) N-14 m/z = 485.19(C₃₅H₂₃N₃ = 485.59) N-15 m/z =434.18(C₃₂H₂₂N₂ = 434.54) N-16 m/z = 434.18(C₃₂H₂₂N₂ = 434.54) N-17 m/z= 511.2(C₃₇H₂₅N₃ = 511.63) N-18 m/z = 561.22(C₄₁H₂₇N₃ = 561.69) N-19 m/z= 587.24(C₄₃H₂₉N₃ = 587.73) N-20 m/z = 511.2(C₃₇H₂₅N₃ = 511.63) N-21 m/z= 511.2(C₃₇H₂₅N₃ = 511.63) N-22 m/z = 511.2(C₃₇H₂₅N₃ = 511.63) N-23 m/z= 511.2(C₃₇H₂₅N₃ = 511.63) N-24 m/z = 587.24(C₄₃H₂₉N₃ = 587.73) N-25 m/z= 435.17(C₃₁H₂₁N₃ = 435.53) N-26 m/z = 435.17(C₃₁H₂₁N₃ = 435.53) N-27m/z = 435.17(C₃₁H₂₁N₃ = 435.53) N-28 m/z = 435.17(C₃₁H₂₁N₃ = 435.53)N-29 m/z = 435.17(C₃₁H₂₁N₃ = 435.53) N-30 m/z = 435.17(C₃₁H₂₁N₃ =435.53) N-31 m/z = 435.17(C₃₁H₂₁N₃ = 435.53) N-32 m/z = 434.18(C₃₂H₂₂N₂= 434.54) N-33 m/z = 485.19(C₃₅H₂₃N₃ = 485.59) N-34 m/z = 511.2(C₃₇H₂₅N₃= 511.63) N-35 m/z = 511.2(C₃₇H₂₅N₃ = 511.63) N-36 m/z = 511.2(C₃₇H₂₅N₃= 511.63) N-37 m/z = 485.19(C₃₅H₂₃N₃ = 485.59) N-38 m/z = 511.2(C₃₇H₂₅N₃= 511.63) N-39 m/z = 485.19(C₃₅H₂₃N₃ = 485.59) N-40 m/z =611.24(C₄₅H₂₉N₃ = 611.75) N-41 m/z = 511.2(C₃₇H₂₅N₃ = 511.63) N-42 m/z =511.2(C₃₇H₂₅N₃ = 511.63) N-43 m/z = 587.24(C₄₃H₂₉N₃ = 587.73) N-44 m/z =587.24(C₄₃H₂₉N₃ = 587.73) N-45 m/z = 587.24(C₄₃H₂₉N₃ = 587.73) N-46 m/z= 561.22(C₄₁H₂₇N₃ = 561.69) N-47 m/z = 511.2(C₃₇H₂₅N₃ = 511.63) N-48 m/z= 587.24(C₄₃H₂₉N₃ = 587.73) N-49 m/z = 485.19(C₃₅H₂₃N₃ = 485.59) N-50m/z = 485.19(C₃₅H₂₃N₃ = 485.59) N-51 m/z = 485.19(C₃₅H₂₃N₃ = 485.59)N-52 m/z = 485.19(C₃₅H₂₃N₃ = 485.59) N-53 m/z = 485.19(C₃₅H₂₃N₃ =485.59) N-54 m/z = 535.2(C₃₉H₂₅N₃ = 535.65) N-55 m/z = 485.19(C₃₅H₂₃N₃ =485.59) N-56 m/z = 485.19(C₃₅H₂₃N₃ = 485.59) N-57 m/z = 561.22(C₄₁H₂₇N₃= 561.69) N-58 m/z = 561.22(C₄₁H₂₇N₃ = 561.69) N-59 m/z =561.22(C₄₁H₂₇N₃ = 561.69) N-60 m/z = 637.25(C₄₇H₃₁N₃ = 637.79) N-61 m/z= 561.22(C₄₁H₂₇N₃ = 561.69) N-62 m/z = 561.22(C₄₁H₂₇N₃ = 561.69) N-63m/z = 637.25(C₄₇H₃₁N₃ = 637.79) N-64 m/z = 637.25(C₄₇H₃₁N₃ = 637.79)N-65 m/z = 637.25(C₄₇H₃₁N₃ = 637.79) N-66 m/z = 485.19(C₃₅H₂₃N₃ =485.59) N-67 m/z = 485.19(C₃₅H₂₃N₃ = 485.59) N-68 m/z = 611.24(C₄₅H₂₉N₃= 611.75) N-69 m/z = 485.19(C₃₅H₂₃N₃ = 485.59) N-70 m/z =485.19(C₃₅H₂₃N₃ = 485.59) N-71 m/z = 611.24(C₄₅H₂₉N₃ = 611.75) N-72 m/z= 485.19(C₃₅H₂₃N₃ = 485.59) N-73 m/z = 485.19(C₃₅H₂₃N₃ = 485.59) N-74m/z = 561.22(C₄₁H₂₇N₃ = 561.69) N-75 m/z = 485.19(C₃₅H₂₃N₃ = 485.59)N-76 m/z = 485.19(C₃₅H₂₃N₃ = 485.59) N-77 m/z = 611.24(C₄₅H₂₉N₃ =611.75) N-78 m/z = 611.24(C₄₅H₂₉N₃ = 611.75) N-79 m/z = 485.19(C₃₅H₂₃N₃= 485.59) N-80 m/z = 485.19(C₃₅H₂₃N₃ = 485.59) N-81 m/z =485.19(C₃₅H₂₃N₃ = 485.59) N-82 m/z = 485.19(C₃₅H₂₃N₃ = 485.59) N-83 m/z= 535.2(C₃₉H₂₅N₃ = 535.65) N-84 m/z = 535.2(C₃₉H₂₅N₃ = 535.65) N-85 m/z= 585.22(C₄₃H₂₇N₃ = 585.71) N-86 m/z = 535.2(C₃₉H₂₅N₃ = 535.65) N-87 m/z= 585.22(C₄₃H₂₇N₃ = 585.71) N-88 m/z = 585.22(C₄₃H₂₇N₃ = 585.71) N-89m/z = 611.24(C₄₅H₂₉N₃ = 611.75) N-90 m/z = 611.24(C₄₅H₂₉N₃ = 611.75)N-91 m/z = 585.22(C₄₃H₂₇N₃ = 585.71) N-92 m/z = 611.24(C₄₅H₂₉N₃ =611.75) N-93 m/z = 687.27(C₅₁H₃₃N₃ = 687.85) N-94 m/z = 611.24(C₄₅H₂₉N₃= 611.75) N-95 m/z = 511.2(C₃₇H₂₅N₃ = 511.63) N-96 m/z = 611.24(C₄₅H₂₉N₃= 611.75) N-97 m/z = 561.22(C₄₁H₂₇N₃ = 561.69) N-98 m/z =587.24(C₄₃H₂₉N₃ = 587.73) N-99 m/z = 663.27(C₄₉H₃₃N₃ = 663.82) N-100 m/z= 713.28(C₅₃H₃₅N₃ = 713.88) N-101 m/z = 575.2(C₄₁H₂₅N₃O = 575.67) N-102m/z = 601.22(C₄₃H₂₇N₃O = 601.71) N-103 m/z = 700.26(C₅₁H₃₂N₄ = 700.85)N-104 m/z = 701.25(C₅₁H₃₁N₃O = 701.83) N-105 m/z = 667.21(C₄₇H₂₉N₃S =667.83) N-106 m/z = 541.16(C₃₇H₂₃N₃S = 541.67) N-107 m/z =612.23(C₄₄H₂₈N₄ = 612.74) N-108 m/z = 562.22(C₄₀H₂₆N₄ = 562.68) N-109m/z = 689.26(C₄₉H₃₁N₅ = 689.82) N-110 m/z = 639.24(C₄₅H₂₉N₅ = 639.76)N-111 m/z = 701.25(C₅₁H₃₁N₃O = 701.83) N-112 m/z = 631.17(C₄₃H₂₅N₃OS =631.75) N-113 m/z = 625.22(C₄₅H₂₇N₃O = 625.73) N-114 m/z =591.18(C₄₁H₂₅N₃S = 591.73) N-115 m/z = 687.27(C₅₁H₃₃N₃ = 687.85) N-116m/z = 701.25(C₅₁H₃₁N₃O = 701.83) N-117 m/z = 619.3(C₄₅H₃₇N₃ = 619.81)N-118 m/z = 601.25(C₄₄H₃₁N₃ = 601.75) N-119 m/z = 667.23(C₄₇H₂₉N₃O₂ =667.77) N-120 m/z = 540.24(C₃₉H₂₀D₅N₃ = 540.68) N-121 m/z =521.17(C₃₅H₂₁F₂N₃ = 521.57) N-122 m/z = 510.18(C₃₆H₂₂N₄ = 510.6) N-123m/z = 652.23(C₄₆H₂₈N₄O = 652.76) N-124 m/z = 527.24(C₃₈H₂₉N₃ = 527.67)N-125 m/z = 535.2(C₃₉H₂₅N₃ = 535.65) N-126 m/z = 535.2(C₃₉H₂₅N₃ =535.65) N-127 m/z = 535.2(C₃₉H₂₅N₃ = 535.65) N-128 m/z = 535.2(C₃₉H₂₅N₃= 535.65) N-129 m/z = 587.24(C₄₃H₂₉N₃ = 587.73) N-130 m/z =612.23(C₄₄H₂₈N₄ = 612.74) N-131 m/z = 561.22(C₄₁H₂₇N₃ = 561.69) N-132m/z = 687.27(C₅₁H₃₃N₃ = 687.85) N-133 m/z = 663.27(C₄₉H₃₃N₃ = 663.82)N-134 m/z = 601.22(C₄₃H₂₇N₃O = 601.71) N-135 m/z = 617.19(C₄₃H₂₇N₃S =617.77) N-136 m/z = 752.29(C₅₅H₃₆N₄ = 752.92) N-137 m/z =651.23(C₄₇H₂₉N₃O = 651.77) N-138 m/z = 677.25(C₄₉H₃₁N₃O = 677.81) N-139m/z = 541.16(C₃₇H₂₃N₃S = 541.67) N-140 m/z = 750.28(C₅₅H₃₄N₄ = 750.91)N-141 m/z = 707.24(C₅₉H₃₃N₃S = 707.9) N-142 m/z = 651.23(C₄₇H₂₉N₃O =651.77) N-143 m/z = 617.19(C₄₃H₂₇N₃S = 617.77) N-144 m/z =667.21(C₄₇H₂₉N₃S = 667.83) N-145 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) N-146m/z = 767.26(C5₅₅H₃₃N₃O₂ = 767.89) N-147 m/z = 647.15(C₄₃H₂₅N₃S₂ =647.81) N-148 m/z = 690.24(C₄₉H₃₀N₄O = 690.81) N-149 m/z =511.2(C₃₇H₂₅N₃ = 511.63) N-150 m/z = 587.24(C₄₃H₂₉N₃ = 587.73) N-151 m/z= 511.2(C₃₇H₂₅N₃ = 511.63) N-152 m/z = 511.2(C₃₇H₂₅N₃ = 511.63) N-153m/z = 511.2(C₃₇H₂₅N₃ = 511.63) N-154 m/z = 511.2(C₃₇H₂₅N₃ = 511.63)N-155 m/z = 511.2(C₃₇H₂₅N₃ = 511.63) N-156 m/z = 561.22(C₄₁H₂₇N₃ =561.69) N-157 m/z = 485.19(C₃₅H₂₃N₃ = 485.59) N-158 m/z =561.22(C₄₁H₂₇N₃ = 561.69) N-159 m/z = 611.24(C₄₅H₂₉N₃ = 611.75) N-160m/z = 561.22(C₄₁H₂₇N₃ = 561.69) N-161 m/z = 535.2(C₃₉H₂₅N₃ = 535.65)N-162 m/z = 561.22(C₄₁H₂₇N₃ = 561.69) N-163 m/z = 611.24(C₄₅H₂₉N₃ =611.75) N-164 m/z = 561.22(C₄₁H₂₇N₃ = 561.69) N-165 m/z =485.19(C₃₅H₂₃N₃ = 485.59) N-166 m/z = 561.22(C₄₁H₂₇N₃ = 561.69) N-167m/z = 611.24(C₄₅H₂₉N₃ = 611.75) N-168 m/z = 561.22(C₄₁H₂₇N₃ = 561.69)N-169 m/z = 485.19(C₃₅H₂₃N₃ = 485.59) N-170 m/z = 561.22(C₄₁H₂₇N₃ =561.69) N-171 m/z = 535.2(C₃₉H₂₅N₃ = 535.65) N-172 m/z = 535.2(C₃₉H₂₅N₃= 535.65) N-173 m/z = 561.22(C₄₁H₂₇N₃ = 561.69) N-174 m/z =637.25(C₄₇H₃₁N₃ = 637.79) N-175 m/z = 587.24(C₄₃H₂₉N₃ = 587.73) N-176m/z = 687.27(C₅₁H₃₃N₃ = 687.85) N-177 m/z = 637.25(C₄₇H₃₁N₃ = 637.79)N-178 m/z = 561.22(C₄₁H₂₇N₃ = 561.69) N-179 m/z = 499.17(C₃₅H₂₁N₃O =499.57) N-180 m/z = 541.16(C₃₇H₂₃N₃S = 541.67) N-181 m/z =611.24(C₄₅H₂₉N₃ = 611.75) N-182 m/z = 687.27(C₅₁H₃₃N₃ = 687.85) N-183m/z = 676.26(C₄₉H₃₂N₄ = 676.82) N-184 m/z = 525.22(C₃₈H₂₇N₃ = 525.66)

Evaluation of Manufacture of Organic Light Emitting Diode [Example 1] to[Example 30] Manufacture and Evaluation of Red Organic Light EmittingDiode (Emitting Layer Mixed Phosphorescent Host)

First, on an ITO layer (anode) formed on a glass substrate,4,4′,4″-Tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter will beabbreviated as 2-TNATA) film was vacuum-deposited as a hole injectionlayer to form a thickness of 60 nm. Subsequently,N,N′-Bis(1-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4,4′-diamine(hereinafter abbreviated as NPB) was vacuum deposited to form a holetransport layer with a thickness of 60 nm.

The compound of the present invention (described in Table 5) representedby Formula 1 (first host compound) and Formula 2 (second host compound)as a host on the hole transport layer was mixed at 5:5, and as thedopant, an emitting layer having a thickness of 30 nm was deposited onthe hole transport layer by doping (piq)2Ir(acac)[bis-(1-phenylisoquinolyl) iridium(III)acetylacetonate] with 5% weight.

(1,1′-bisphenyl)-4-oleato)bis(2-methyl-8-quinolinoleato) aluminum(abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm as ahole blocking layer, and Tris(8-hydroxyquinolinato)aluminium(abbreviated as Alq3) was deposited to a thickness of 40 nm as anelectron transport layer. Thereafter, as an electron injection layer,LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm,subsequently, Al was deposited to a thickness of 150 nm and used as acathode to manufacture an organic electronic element.

Comparative Example 1

An organic electronic element was manufactured in the same manner as inExample 1, except that Comparative Compound 2 was used as a single host.

Comparative Example 2 and Comparative Example 3

An organic electronic element was manufactured in the same manner as inExample 1, except that either P-81 or N-91 was used as a single host.

Comparative Example 4

An organic electronic element was manufactured in the same manner as inExample 1, except that Comparative Compound 1 and Comparative Compound 3were mixed and used as a host.

Comparative Example 5

An organic electronic element was manufactured in the same manner as inExample 1, except that Comparative Compound 2 and N-137 were mixed andused as a host.

Comparative Example 6

An organic electronic element was manufactured in the same manner as inExample 1, except that P-81 and Comparative Compound 3 were mixed andused as a host.

TABLE 5 Current First Second Density Brightness Efficiency compoundcompound Voltage (mA/cm²) (cd/m²) (cd/A) Lifespan comparativecomparative — 6.3 22.3 2500.0 11.2 49.8 example 1 compound2 comparativeP-81 — 6.1 18.0 2500.0 13.9 55.4 example 2 comparative N-91 — 5.9 17.22500.0 14.5 63.0 example 3 comparative comparative comparative 5.7 11.52500.0 21.6 57.1 example 4 compound1 compound3 comparative comparative N-137 5.7 8.7 2500.0 28.6 71.9 example 5 compound2 comparative P-81comparative 5.5 10.5 2500.0 23.9 75.9 example 6 compound3 example1 P-24N-65 5.2 7.0 2500.0 35.9 122.1 example2 P-82 N-65 5.0 6.4 2500.0 38.8130.7 example3 P-95 N-65 5.1 6.9 2500.0 36.3 124.3 example4  P-114 N-655.2 7.2 2500.0 34.9 122.2 example5  P-117 N-65 5.1 7.0 2500.0 35.8 111.4example6 P-24 N-86 5.1 6.9 2500.0 36.4 113.5 example7 P-82 N-86 4.9 6.22500.0 40.5 125.3 example8 P-95 N-86 4.9 6.3 2500.0 39.4 123.1 example9 P-114 N-86 5.0 6.5 2500.0 38.6 117.6 example10  P-117 N-86 4.9 6.32500.0 39.9 105.9 example11 P-24 N-93 5.0 7.0 2500.0 35.6 107.0example12 P-82 N-93 4.9 6.2 2500.0 40.6 117.2 example13 P-95 N-93 5.06.3 2500.0 39.9 115.2 example14  P-114 N-93 5.0 6.6 2500.0 38.0 105.3example15  P-117 N-93 5.0 6.4 2500.0 38.9 104.0 example16 P-24  N-1135.1 6.6 2500.0 37.8 120.4 example17 P-82  N-113 4.9 6.1 2500.0 41.0124.0 example18 P-95  N-113 5.0 6.3 2500.0 39.8 124.5 example19  P-114 N-113 5.1 6.8 2500.0 36.7 120.5 example20  P-117  N-113 5.0 6.3 2500.039.5 115.2 example21 P-24  N-129 5.1 6.9 2500.0 36.2 118.0 example22P-82  N-129 4.9 6.2 2500.0 40.6 118.7 example23 P-95  N-129 4.9 6.82500.0 36.8 116.5 example24  P-114  N-129 5.0 7.3 2500.0 34.3 114.7example25  P-117  N-129 4.9 6.4 2500.0 38.9 107.0 example26 P-24  N-1585.1 6.2 2500.0 40.1 97.9 example27 P-82  N-158 4.8 5.9 2500.0 42.5 96.7example28 P-95  N-158 4.9 6.0 2500.0 41.8 97.6 example29  P-114  N-1585.1 6.4 2500.0 39.3 99.3 example30  P-117  N-158 4.9 6.0 2500.0 41.799.3

As can be seen from the results of Table 5, when the material for anorganic electroluminescent device of the present invention representedby Formula 1 and Formula 2 is mixed and used as a phosphorescent host(example 1-30); the efficiency and lifespan were significantly improvedcompared to devices using a single material (Comparative Examples 1-3)or devices mixed with a comparative compound (Comparative Examples 4-6).

That is, the device characteristics of Comparative Examples 4 to 6 usedas a host by mixing two kinds of compounds were improved compared to thedevice characteristics of Comparative Examples 2 and 3 in which thecompound of the present invention represented by Formula 1 or Formula 2was used as a single host respectively, and in the case of the presentinvention using a mixture of substances corresponding to Formulas 1 and2 of the present invention as a host, the efficiency and lifespan aresignificantly improved rather than Comparative Examples 4 to 6,

When using a mixture as in the present invention, not only electrons andholes are moved through the energy level of each material, but alsoefficiency and lifespan are increased due to movement or energy transferof electrons and holes due to mixing. As a result, when the compoundrepresented by Formula 1 having fast hole characteristics and thecompound represented by Formula 2 having strong electronic propertiesare mixed and used as a host, as in the present invention, thecharacteristics of the device are maximized because of a goodelectrochemical synergy effect.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment. The scope of thepresent invention shall be construed on the basis of the accompanyingclaims, and it shall be construed that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentinvention.

BRIEF DESCRIPTION OF THE DRAWINGS 100, 200, 300: organic electronic 110:the first electrode element 120: hole injection layer 130: holetransport layer 140: emitting layer 150: electron transport layer 160:electron injection layer 170: second electrode 180: light efficiencyenhancing 210: buffer layer Layer 220: emitting-auxiliary layer 320:first hole injection layer 330: first hole transport layer 340: firstemitting layer 350: first electron transport layer 360: first chargegeneration layer 361: second charge generation 1ayer 420: second holeinjection layer 430: second hole transport layer 440: second emittinglayer 450: second electron transport layer CGL: charge generation layerST1: first stack ST1: second stack

What is claimed is:
 1. A compound selected from the group consisting ofthe following compounds:


2. An organic electric element comprising a first electrode; a secondelectrode; and an organic material layer formed between the firstelectrode and the second electrode, wherein the organic material layercomprises an hole injection layer, an hole transport layer, an emittingauxiliary layer and an emitting layer, and the organic material layercomprises the compound of claim
 1. 3. The organic electric elementaccording to claim 2, wherein the compound is included in at least oneof the hole injection layer, the hole transport layer, the emittingauxiliary layer and the emitting layer, as a single compound or amixture of two or more of the compounds having different structures. 4.The organic electric element according to claim 3, wherein the compoundis included in the emitting layer.
 5. The organic electric elementaccording to claim 2, further comprising a light efficiency enhancinglayer formed on one side of the first electrode and/or one side of thesecond electrode, the side being located opposite to the organicmaterial layer.
 6. An electronic device comprising: a display deviceincluding the organic electronic element of claim 2; and a control unitfor driving the display device.
 7. The organic electronic element ofclaim 6, wherein the organic electronic element is at least one of anOLED, an organic solar cell, an organic photo conductor, an organictransistor and an element for monochromic or white illumination.